Water → [1-(phenylsulfonyl)-3-pyrrolidinyl]-carbamic acid, 1,1-dimethylethyl Ester

HRID 38285Notes

Reaction equation

HRID 38285 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH2:12][NH:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:21]1([S:27](Cl)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>C1COCC1.CCOCC>[C:21]1([S:27]([N:11]2[CH2:12][CH2:13][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:10]2)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamate

Product 1

HCID 86631068[1-(phenylsulfonyl)-3-pyrrolidinyl]-carbamic acid, 1,1-dimethylethyl Ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(tert-butoxycarbonylamino)pyrrolidine (0.7 g) in THF (20 ml) cooled to 0° C. was added triethylamine (0.52 ml) followed by the addition of benzenesulfonyl chloride (0.48 ml) dropwise over 5 minutes. After stirring for 2 hours the mixture was poured into water and the organics extracted into ether. The ether extractions were combined, washed with brine, dried (MgSO4) and concentrated in vacuo to give crude material. Trituration with ether gave subtitle compound as a colourless solid (0.9 g).

Workup

  1. extractionthe organics extracted into ether
  2. extractionThe ether extractions
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give crude material

Sources & evidence

ORD record
ord-f31e532c9bd8475da309965169bbd376
Source dataset
uspto-grants-2013_09
Patent number
US08524715B2

Reaction notes

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